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Vacation rental beach houses in Anna Maria

Vacation rental beach houses in Anna Maria

Book beachfront vacation rental houses, cottages, and more on Airbnb

Top-rated houses in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness, and more.

Luxury 3BR/3BA, Private Heated Pool, Beach
SUPERHOSTEntire house · 6 guests · 5 beds · 3 baths
Luxury 3BR/3BA, Private Heated Pool, Beach

Renovated and professionally decorated single family home that sleeps 8. 3 bedrooms and 3 full bathrooms. Living room with pullout couch as well as games, books and movie library. Luxurious heated pool with waterfall and Tiki table in private tropical backyard. Large covered lanai with TV, mini-fridge, granite counter for food preparation and gas BBQ. Large size Washer/Dryer. 4 minute easy stroll to beach. Attached garage. Low traffic street. Tons of toys as well as pool and beach supplies.

What guests are saying:

“In the midst of a global pandemic we were itching to get away having been quarantined for months. This villa was EXACTLY what was needed. We are a family of 4 and the villa was beyond accommodating for all of us. The hosts have thought about every conceivable detail in terms of what they provide in terms of supplies, information, contact details, restaurants, tips, etc. They were also incredibly responsive and engaged in trying to ensure we had a very special time. We are fortunate to be able to travel the world and our original trip to Belize during this time was cancelled. Not a moment of sadness entered our minds with staying here. Cannot rate this high enough!”

5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house · 8 guests · 5 beds · 2 baths
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

What guests are saying:

“This home was a perfect getaway for our family. There were seven of us and the accommodations were very comfortable with the four rooms provided. The home is lovely & actually quite spacious-laid out very well. We never felt cramped. The backyard oasis was a wonderful escape and made for a fun amenity for our family. Had a tropical island feel which made the experience even more fun. Location is also perfect as you are just a 3 to 4 minute walk from the beach. Also very close to anything you need- grocery store, ice cream shop. Also appreciate the beach cart, chairs, tent, umbrella & floats. You really don’t need to bring anything with you. Highly recommend!!”

Cozy Beachhouse 800 steps to beach
SUPERHOSTEntire house · 3 guests · 1 bed · 1 bath
Cozy Beachhouse 800 steps to beach

This beautiful home is only 800 steps from one of the most beautiful beaches in Southwest Florida. Great getaway for couples. Amazing restaurants and entertainment very close. Free trolley, endless things to do: kayaking, sunbathing, and relaxing.

What guests are saying:

“This Airbnb was perfect! It was very clean, spacious enough for me and my husband, had all the amenities and comforts of home. The bed was very comfortable which is always important and cold AC! Location location was this Airbnb, One block from the beach, walking distance to cafés and restaurants, and we brought our bikes and rode all over the island visiting stores and restaurants. I would definitely stay here again.”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular house amenities in Anna Maria

  • Pool
  • Pets allowed
  • Air conditioning
  • Kitchen
  • Wifi

Cottages in Anna Maria

Cozy Cottage by the Beach sleeps 6 - Seascape
SUPERHOSTEntire cottage
Cozy Cottage by the Beach sleeps 6 - Seascape
Price:R2,723 ZAR / night
Turtle Cottage - Anna Maria Island
SUPERHOSTEntire cottage
Turtle Cottage - Anna Maria Island
Price:R3,617 ZAR / night
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
SUPERHOSTEntire cottage
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
Price:R3,100 ZAR / night
'Elegance' 100 Steps from the Beach
Entire cottage
'Elegance' 100 Steps from the Beach
Price:R5,535 ZAR / night
Becker's Beach Bungalow
SUPERHOSTEntire cottage
Becker's Beach Bungalow
Price:R2,636 ZAR / night
Beach Cottage with private garden
SUPERHOSTEntire cottage
Beach Cottage with private garden
Price:R2,548 ZAR / night
Rest & Relax — Just One House Off The Beach
SUPERHOSTEntire cottage
Rest & Relax — Just One House Off The Beach
Price:R2,924 ZAR / night
MorSea Cottage: A Beachside Oasis
Entire cottage
MorSea Cottage: A Beachside Oasis
Price:R5,535 ZAR / night
Unwind SUNSHINE..tropical oasis, heated pool
Entire cottage
Unwind SUNSHINE..tropical oasis, heated pool
Price:R10,542 ZAR / night
50 Steps to Beach🏖.  Hot Tub! 1bd modern cottage🏝
SUPERHOSTEntire cottage
50 Steps to Beach🏖. Hot Tub! 1bd modern cottage🏝
Price:R4,129 ZAR / night
Palm Cottage in North Longboat Key
SUPERHOSTEntire cottage
Palm Cottage in North Longboat Key
Price:R1,493 ZAR / night
Dog-friendly cottage w/ island views, shared pool & private patio - beach nearby
Entire cottage
Dog-friendly cottage w/ island views, shared pool & private patio - beach nearby
Price:R2,969 ZAR / night
Show all

Pet-friendly houses

5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
Price:R5,896 ZAR / night
Twin Palms: Big house steps to beach, private pool
SUPERHOSTEntire house
Twin Palms: Big house steps to beach, private pool
Price:R5,474 ZAR / night
#1-Poolside 2br KING--Sleeps 6--MINS to BEACH
SUPERHOSTPrivate room
#1-Poolside 2br KING--Sleeps 6--MINS to BEACH
Price:R3,363 ZAR / night
Dog-friendly home with private pool, great location near beach, shopping, dining
Entire house
Dog-friendly home with private pool, great location near beach, shopping, dining
Price:R4,024 ZAR / night
Captain's Quarters at Spinnakers Vacation Cottages
SUPERHOSTEntire house
Captain's Quarters at Spinnakers Vacation Cottages
Price:R5,083 ZAR / night
The Anna Maria Beach Cottage - East
SUPERHOSTEntire house
The Anna Maria Beach Cottage - East
Price:R2,161 ZAR / night
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
Price:R3,497 ZAR / night
⭐250 feet from the beach ⭐
SUPERHOSTEntire house
⭐250 feet from the beach ⭐
Price:R2,053 ZAR / night
Dog friendly oasis with private pool and very close to the beach
Entire house
Dog friendly oasis with private pool and very close to the beach
Price:R4,445 ZAR / night
Anna Maria Island Duplex w/ private pool (side B)
SUPERHOSTEntire house
Anna Maria Island Duplex w/ private pool (side B)
Price:R3,205 ZAR / night
Top-rated Anna Maria, Florida Vacation Rental
SUPERHOSTEntire house
Top-rated Anna Maria, Florida Vacation Rental
Price:R5,823 ZAR / night
Salty Dogs on Anna Maria,  Special Sep 7-14, 19-26
SUPERHOSTEntire house
Salty Dogs on Anna Maria, Special Sep 7-14, 19-26
Price:R6,835 ZAR / night
Show all

Houses with pools

Luxury 3BR/3BA, Private Heated Pool, Beach
SUPERHOSTEntire house
Luxury 3BR/3BA, Private Heated Pool, Beach
Price:R4,302 ZAR / night
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
Price:R5,896 ZAR / night
Discounted 3-Day Escape! Sept 7-10 @ 5-Star House!
SUPERHOSTEntire house
Discounted 3-Day Escape! Sept 7-10 @ 5-Star House!
Price:R4,568 ZAR / night
Happy Island Cottage - Heated Pool
SUPERHOSTEntire house
Happy Island Cottage - Heated Pool
Price:R5,781 ZAR / night
Twin Palms: Big house steps to beach, private pool
SUPERHOSTEntire house
Twin Palms: Big house steps to beach, private pool
Price:R5,474 ZAR / night
#1-Poolside 2br KING--Sleeps 6--MINS to BEACH
SUPERHOSTPrivate room
#1-Poolside 2br KING--Sleeps 6--MINS to BEACH
Price:R3,363 ZAR / night
Sea Vous Play
SUPERHOSTEntire house
Sea Vous Play
Price:R9,224 ZAR / night
Captain's Quarters at Spinnakers Vacation Cottages
SUPERHOSTEntire house
Captain's Quarters at Spinnakers Vacation Cottages
Price:R5,083 ZAR / night
Dog-friendly home with private pool, great location near beach, shopping, dining
Entire house
Dog-friendly home with private pool, great location near beach, shopping, dining
Price:R4,024 ZAR / night
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
SUPERHOSTEntire house
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
Price:R7,593 ZAR / night
Top-rated Anna Maria, Florida Vacation Rental
SUPERHOSTEntire house
Top-rated Anna Maria, Florida Vacation Rental
Price:R5,823 ZAR / night
New Prof Decor-Pool/Spa 5 Mn walk 2 ocean Discount
SUPERHOSTEntire house
New Prof Decor-Pool/Spa 5 Mn walk 2 ocean Discount
Price:R7,969 ZAR / night
Show all

Learn more about Anna Maria

What types of vacation rentals are available in Anna Maria?

Here in Anna Maria, there are plenty of options for places to stay. Here are a few examples:
  • Houses (313 rentals)
  • Cottages (16 rentals)
  • Apartments (15 rentals)

Are there houses that are pet-friendly?

Who doesn’t want pets allowed in their house? Here in Anna Maria, you’ll find 98 houses that are pet-friendly.

What are the top attractions in Anna Maria?

Locals agree that these attractions are worth a visit:
  • Anna Maria Public Beach (225 rentals)
  • Bean Point (74 rentals)
  • Beach Bums Recreational Rentals & Gift Shop (181 rentals)
  • Island Players Inc (184 rentals)

What are some kid-friendly activities in Anna Maria?

Locals agree—these are all great places to take the kids:
  • Anna Maria Public Beach
  • Bean Point
  • Beach Bums Recreational Rentals & Gift Shop
  • Pine Avenue
  • Two Scoops

What are the top places to eat in Anna Maria?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • The Sandbar Restaurant
  • The Waterfront Restaurant
  • Rod and Reel Pier
  • Poppo's Taqueria
  • Two Scoops